


Can't Pretend

by orphan_account



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Alternate Universe- No Supernatural, Cas is pretty flexible with how he dresses, Crossdressing, F/M, M/M, This isn't helping me improve my writing at all, basically writing practice, better tags will be added, if i remember/stop being lazy, someone teach me how to write, the characters in the tags will show up more even if at this point they've only been mentioned
Language: English
Status: In-Progress
Published: 2013-11-11
Updated: 2014-02-16
Packaged: 2018-01-01 03:39:15
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 10,471
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1039913
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Castiel actively avoids categorizing himself as normal, even if he often appears to be so. He fights gender roles by crossdressing, refuses to label his sexuality, and remains socially inept in spite of his person-oriented jobs. He meets (or re-meets, if that college thing counts) Dean Winchester thanks to Sam,  Castiel’s only friend. ...Things kind of spiral from that.</p>
            </blockquote>





	1. Persona Non Grata

**Author's Note:**

> Title taken from the song by Tom Odell. This is my first multi-chapter fic and I'm hoping to keep motivated enough to finish it. Advice and critique is both welcome and adored (even if you only tell me that it's a crap story, that helps me!). Unbeta'd, so all typos and whatnot are my own. If it's something obvious or horrifyingly wrong, let me know! And I don't mean to offend anyone with the way I portray these characters, I merely want to explore aspects of what we know in canon, were they given different lives.

Pariah. It was the word Castiel most favored when describing himself, not that he was ever really given the opportunity to do so. And sure, he most likely had only himself to blame, since his siblings always maintained a sociable persona (admittedly a facade for most of them). Castiel was the one seen as out of place. 

In high school, he’d been a wallflower. Not in the romantic, artistic sense; rather, he was a wallflower in the sense that he was a painfully quiet misanthropist, albeit unintentionally. Then, he had allowed himself freedom in college: experimenting with drugs and alcohol, even working up the nerve for a tattoo. He regretted the latter when he applied for jobs, and was forced to hide the ink scrawl that encircled his left wrist: an old Irish blessing, the words he’d known from a hymn sung at Mass in his youth. He’d hated attending, but his adoptive mother was immensely religious. (Naomi was naive enough to believe God to be benevolent, but Castiel was certain no god would allow for his children to suffer the way many of them did.) In any case, Castiel had loved the song and contemplated getting the tattoo in Gaelic, but settled on Enochian because it held a deeper resonance with his fondness for language. And it reminded him of his parents, neither of which he’d actually known, because they were the ones to give him the name of an Angel. 

Castiel had only two people in his life who he would have considered referring to as friends. The first, Samandriel, was his younger brother. Of course, Castiel couldn’t call Samandriel his friend anymore-- he’d been dead for two years, killed in a car accident on his way home from a study session. Castiel still harbored remorse, knowing that had he offered to pick Samandriel up, his brother might have survived. 

The second person Castiel identified as a friend was Sam Winchester. Sam was a lawyer, fresh-faced and ambitious, with an unrivalled drive to be successful. Castiel was constantly torn between envy and pride. The two had become friends when Castiel was working as a barista at his brother Gabriel’s coffee shop. Apparently, Sam was a regular, because Gabriel had Sam’s order ready before Castiel could even take it. Later, they had run into each other again at the local library, each preparing for midterms. Surprisingly, Sam had remembered him. 

“You work at Gabriel’s place, right? I saw you earlier?”

Castiel was enraptured by Sam’s easygoing charisma, managing to nod and smile awkwardly.

“Gabriel is my older brother,” he’d answered. Sam had nodded thoughtfully. After that, they saw each other so frequently at the coffee shop (Trickster Treat, as Gabriel had insisted on naming the place) that they began studying together. Castiel was fond of Sam, because the other man had never balked at the fact that Castiel sometimes crossdressed or wore make-up, instead being accepting of the fact that Castiel actively avoided conforming to societally-enforced gender roles.

“I feel oppressed, and if combatting it means dressing inventively, so be it,” Castiel had explained one day. “Besides, I like to think I can pull off fishnets.” Sam’s face had been mildly horrified at the last sentence, but he’d laughed when he realized Castiel was kidding. 

“You’d like my brother,” he’d remarked, ruffling his absurdly long hair. (Castiel had once commented that Sam appeared to be combating gender roles himself, through his ‘hair expression.’)

As it turned out, Sam was right. Castiel didn’t place the connection until much later, but he knew exactly who Sam’s brother was: the notorious Dean Winchester. The man in question had been in several of Castiel’s classes, and Castiel had become absolutely smitten in the course of half a semester. The real tragedy was that Dean was gone by the semester’s end, Castiel later learning that Dean had transitioned from business to engineering. 

That, of course, wasn’t until after the night Castiel had accidentally gotten himself into a game of strip poker... the only players being himself, Dean, Benny Lafitte (who was scary good at card games and pool), and Jo Harvelle, a smirking freshman who held her liquor better than anyone else at the party. She was winning and Castiel was losing. Badly.

Dean was a great player, but ultimately lost big time when he got too cocky. That was what resulted in him losing his pants.

What was under those worn jeans was not what Castiel had expected at all. Pale pink, lacy panties were where Castiel had been certain he would find plaid boxers. Dean had flushed once he’d kicked off his pants, pulling his legs up in front of him in a manner that completely contradicted his usually extroverted demeanor. His brow furrowed when he spotted Castiel staring, but Castiel quickly looked away in embarrassment. It seemed they were the only two bothered by it (if one could call it that, in Castiel’s case). Jo had rolled her eyes and Benny had snickered. 

“Sexy,” the bearded man had drawled. “Didn’t think you had the balls to wear those outside of the bedroom, kiddo. Proud of you.” Jo had only shaken her head at that, looking at Castiel with a “what-is-my-life” expression. Castiel had managed a feeble shrug and then looked away, rubbing the back of his neck. He was down to an underwear and undershirt, more exposed than Dean-- but the round’s winner was the one who chose which article of clothing was removed, and Jo had won the round resulting in Dean’s supposed emasculation. 

Dean had avoided Castiel after that, and Castiel never worked up the courage to find the other man and apologize (what for, he wasn’t exactly sure). Then, Dean was gone permanently, and so much else happened in Castiel’s life (those drug experimentations, for instance, and then Samandriel’s death) that he was forced to push the incident out of his mind. 

Until the “much later” part of connecting the name ‘Dean Winchester’ with the idea of ‘Sam’s Brother.’

___________________

Castiel was certain he’d bombed his job interview, but it was too late to go back and correct himself on every stupid thing he’d said. Instead, he returned to his apartment and shucked his nice clothing in favor of jeans and a dark grey henley, something that’d belonged to a past boyfriend at one point but had been passed down to Castiel after the break up. At least it looked good on him. 

Once he was dressed, he walked the few blocks from his apartment building to Trickster Treats, just in time to find Sam sitting and looking over a newspaper: the epitome of the American male, Castiel thought in amusement.

“Hello, Sam,” he greeted, sliding into the chair opposite his friend. Sam looked up in surprise, then broke into a grin. 

“Hey, Cas, what’ve you been up to? I haven’t seen you in forever, but Gabe said you had a job interview today. How’d it go?”

Castiel sighed. “I’m fairly confident that it went terribly. I can’t say it was all too much of a loss, though. Zachariah Adler-- the company’s manager-- seemed to be rather queer-phobic and...unpleasant. I don’t think I’d have enjoyed working for him.”

Sam nodded thoughtfully. “Well, you win some, you lose some,” he told the other man optimistically. “Oh, and I’ve been thinking. I’ve known you since before you graduated. It’s been years, man. I mean, I know we don’t hang out or anything, really, but I feel like I owe you dinner at my place, at least. I mean, I think you and my brother would get along great, too.”

In so long of knowing each other, Cas had obviously concluded that Sam’s brother was a Dean Winchester, but he’d remained in denial of the fact that it could be the Dean Winchester. After all, Dean was a generic enough name… and Winchester? Well, maybe less so, but Cas had met Dean in New York, and this was California. (Besides, Sam had said his brother went to college in Kansas.) Yeah, denial was a major factor.

Castiel blinked back into focus, realizing what Sam had proposed and realizing that the incurable curiosity regarding Sam’s enigmatic brother could be solved soon, if he accepted. 

“I--” he began, unsurely. He chewed his lip and shrugged. “That would be lovely, Sam. I’m certainly intrigued by the prospect of finally meeting your brother.” 

“Great!” Sam’s grin could blind people, Castiel was fairly certain. “How’s Friday? If that’s too short notice, I can give you another day when I see you again, or I can text you.”

“Oh,” Castiel mumbled, baffled. “Friday would be perfect; normally I order take out. Thank you again.”

“Of course, Cas! I’ve been meaning to have you over for awhile, I’m sorry I’m only getting to it now.” Sam took out his cell phone and typed rapidly. “I texted you our address,” he explained. “Hopefully I can get Dean to cook, because he’s fantastic. If I end up cooking, I’m sorry in advance.” He looked sincerely apologetic, and Castiel wondered if he should be concerned. 

“No need to apologize,” he assured Sam (and himself, inwardly). “I’m sure the food will be enjoyable regardless of who cooks.”

Sam merely laughed at that. “Yeah, you better pray for that to be true,” he told Cas easily. Then he pushed back his chair, standing up. “Well, I have to get to work. We’ve got a fun little breaking and entering case going, and I want to hurry up and close it. You know how it is.” Sam shrugged, wearing a what-can-you-do face and a slightly remorseful smile. Then he was gone, along with his newspaper and coffee. 

Castiel recalled that when he’d first met Sam, he’d been disappointed to learn the other man was heterosexual. Looking back, the idea of dating Sam was laughable. (Not that they wouldn’t make a cute couple… but Sam was so in love with the girl Jess that he’d brought to the coffee shop a few times, the idea of Castiel having Sam instead made him guilty. He was glad they were friends, though, of course.)

Cas stood up a moment later, making his way to the counter. His brother turned around and looked up, breaking out into his usual lopsided smirk.

“Baby bro,” he greeted. “What can I do for you?” 

Castiel resisted the urge to roll his eyes. “I wanted to offer to pick up the Sunday shift, since I know you were hoping to fornicate with Kali.”

Gabriel made a face. “Come on, when you say it like that you suck out the sexy. Gross. And yeah, actually, that’d be awesome. You could use the money, I bet, and I could use the sexy time.”

This time, Castiel did roll his eyes. “I’m glad I could help you out. And please refrain from calling me”--Castiel formed air quotes with his fingers, sour--“‘baby bro’ from now on.”

“Haha, not on your life, kiddo. Now go back home and enjoy your day, or go see if you can pick up an extra shift at that pretentious restaurant you wait at.”

Castiel scowled. “It’s not pretentious. Balthazar simply has high standards. Do you blame him? It’s not easy running a restaurant. And he was kind enough to hire me in spite of the fact that we first met whilst I was in a floral magenta skirt.” 

“I’m betting it’s ‘cause your boss is the kinkiest person alive. He probably got off on it. But whatever. The guy’s okay in my book, it’s the way the place is run that’s pretentious. The water curtain centerpiece? Why is there a fountain in there? And what the hell is with the koi fish floating around in the pool the fountain’s coming out of? It’s ridiculous.”

“You’re one to talk. I hate to be the one to tell you, but your entire coffee shop is painted cotton candy pink and highlighter yellow. Luckily, all of your accent pieces are lime green to balance it out.” Castiel’s sardonic retort surprised Gabriel enough to make the man laugh.

“Get out of here, kid. Do what I said or take a day to relax.”  
___________________

“Hey, Dean?” Sam’s voice came from the hall. Good, he was home for dinner, by some freak miracle.

“What’s up?” Dean asked from the kitchen, where he was sauteing onions. “Hope you don’t mind fajitas, by the way. Got groceries and the peppers were cheap.”

“Smells delicious,” Sam told his brother as he came into the kitchen, dropping his messenger back onto the table. “We finally closed that stupid case. Another client’s gotten mixed up in some drug-related stuff, though, so I probably won’t be home tomorrow till ten or eleven. We’re gonna dig up some defense evidence and whatever. The usual.” 

Dean snorted. “Sounds fun,” he said. “Now set the table, nerd. Dinner’s gonna be ready in ten.”

“Yeah, yeah,” Sam kicked off his shoes and loosened his tie, moving to where the napkins were tucked away in their holder on the counter. “I hope you don’t mind, I invited a friend of mine to dinner on Friday… He’s really neat, I’ve been meaning to introduce you two for, like, ever.” 

Dean groaned. “Why?” he asked. “I mean, I’m sure all your law friends are great-- Ash is golden, that’s for sure, but I’m fine. I don’t need to have a crazy-ass amount of friends like you to live, man.”

Sam pulled a bitchface so fast Dean wondered if it would freeze that way. “Come on, Dean. All you’ve done since dad died is work and cook, sometimes getting wasted or laid. That’s not the healthiest way to live. Besides, Cas is really interesting! Just… don’t be weirded out.”

“Why? Is something wrong with him? Is he handicapped? I don’t have a problem with that, Sam, I’m not that douchey.” 

“No, I know you’re not as much of a dick as you pretend to be. And, it’s not that…” Sam trailed off, running a hand through his hair and shrugging. “You won’t be bothered if… okay, just please don’t react if he wears something you don’t really expect him to be wearing.”

“Jesus, Sammy! Like what? Is he a nudist?” Dean asked, pulling a face. Sam scowled.

“No, he just-- he crossdresses sometimes, okay?” Sam looked at Dean then, frozen. Then, quickly, he continued, “it’s not a big deal. He might dress ‘normally’”--Dean could hear the air quotes, even though Sam didn’t make them with his fingers-- “or he might wear, I don’t know, a dress or something. Please don’t be weird about it or let it cloud your judgement. You can ask him about it but don’t be an ass.” 

Dean looked at Sam curiously, but nodded. “I won’t, it’s cool. How did you even become friends with this guy, though?”

“Ran into him at Gabe’s shop. They’re brothers. We became friends when he helped me with some studying stuff. He’s-- he’s really cool, actually.”

Dean wanted to ask why he was only learning about this ‘Cas’ guy now, but he figured he’d just rib the man in question on Friday. He shrugged. “Fine by me. Already planned dinner though, so I hope he’s not a vegan.”

“Don’t worry,” Sam assured his brother. “He’s not.”

Dean refrained from questioning the I-know-something tone Sam had used when he answered, instead shooing his brother from the stove and repeating his command to set the damn table.


	2. Ex Animo

Castiel was determined to make a good impression. Based on how Sam has spoken of his brother, clearly Dean was important to him. And if Sam wanted Dean to meet Castiel, then Cas knew it was necessary for the encounter to run smoothly… Which meant acting ‘normal.’ (Castiel himself insisted that the term was relative, hating the idea of being confined by the term and its synonyms: typical, generic, ordinary, standard. Castiel liked to imagine he was none of those things, which was occasionally problematic.) 

He wanted to wear something nice. Not just “clean pair of pants” nice, either. A nice skirt or a pretty blouse kind of nice, or dress slacks and a vest perhaps.

Castiel had ventured to an outlet recently, and he’d been meaning to find an excuse to wear the pleated skirt he’d found. It was indigo, soft and nice for autumn weather… but it was still a skirt, and Castiel still had no idea how open-minded Dean was, regardless of how highly Sam spoke of him. 

He decided to text Sam.

//Would it be in poor taste to wear a skirt to dinner? -4:56 pm

Sam was quick to reply, luckily for Cas.  
\--Dean’s pretty cool, I wouldn’t worry too much. It’s totally your choice & don’t conform just bc you’re worried about him, k? See you soon? -4:59 pm

//Thank you -5:01 pm

\--Np Cas :) -5:03 pm

Castiel took comfort in Sam’s advice, but still wondered whether he could take his word as fact. He settled instead on wearing an oversized graphic sweater and jeans, reasoning that it was a gender-neutral outfit. At the last second, he added a headband. Why not? It was only an accessory, and Castiel really only wanted Dean’s approval because he liked being friends with Sam. 

He took an unopened bottle of wine (sent to him from his overbearing mother as a birthday gift two months prior) from the recesses of his pantry, then closed his door and made a beeline to the elevator. Living on the fourth floor had no perks, he’d learned long before.  
____________________

“Sam, I swear to god if you leave me with him alone--” Dean warned, glaring at the pasta he was pouring into the boiling pot of water before him. 

“Relax! Jesus, Dean,” Sam jumped in before Dean could voice the rest of his threat. “I’ll be around until six-thirty, I’m picking Jess up at seven, okay? Will you chill? He’ll probably leave before me, or at the same time as me. Besides, you guys will probably get along fine even if I’m not there.” He shrugged. 

“Why did you plan your date to be today, anyways? You’re the one who invited ‘Cas’ over.” Dean said the other man’s name vehemently waving a spoon to emphasize. “Not me. How come you get to duck out?”

“It’s not like that Dean, I swear. This is the only time we’re both free for two weeks, and I really wanted to see her again.”

“You’ve been on three dates with this chick, and technically you aren’t free tonight, asshat.” Dean pointed out. 

Before Sam could argue his case, his cellphone vibrated. He pulled it from his pocket.

//I’m here. -5:37 pm

“Cas is here, so shut up and behave,” Sam instructed, texting his friend back quickly.

\--Buzzing you in now, come on up. 2nd floor. -5:37 pm

He ignored Dean’s indignant “hey!” and left the kitchen. A minute later, someone knocked softly on the door. 

“Hey, Cas! Come on in, sorry it’s kind of messy,” Sam waved in his friend enthusiastically, gesturing to the precariously stacked papers that littered various surfaces. 

“It’s fine,” Castiel assured Sam. “The life of a lawyer is a hectic one, I imagine.” Sam laughed, nodding in agreement. 

“Yeah, speaking of hectic,” he added hesitantly. “God, I hate to do this to you, but I have a date with Jess tonight and I’m gonna have to duck out at six-thirty. I’m so sorry, man, it wasn’t really well thought out and--”

“Sam,” Cas interrupted. “That’s fine, I’ll leave when you do and it will be fine. I’m flattered you were even interested in having me over for dinner.”

“Yeah, sure. Thanks so much for understanding. Nice headband, by the way. Really… cute.” Sam finished with a sheepish grin.

“Thank you. Is there anything I can do to help with dinner?”

Sam shook his head. “Table’s set and Dean’s in the kitchen. Dinner’s gonna be ready really soon. Can I get you a drink?”

Castiel offered Sam the bottle of wine and smiled. “A drink would be nice.”

“What can I get you? We’ve got beer in the fridge, we could open your wine… Dean’s a Dr. Pepper fiend so there’s plenty of that, and water.”

“A beer sounds great, thanks.” Castiel smiled at Sam. 

_______________________

Dean was in the kitchen, straining the pasta, when he heard Cas speak. And fuck, he recognized that rough, low voice. Cas, Cas, Cas.

“You didn’t tell me that ‘Cas’ was short for Castiel,” he hissed, grabbing his brother’s arm as Sam entered the kitchen. 

“Jesus!” Sam yelped, startled. Then he frowned at Dean. “How’d you deduce that one?” he asked curiously. His brother grimaced.

“None of your business.” he answered instantly, turning away again. “Forget it.”

Castiel Novak, the boy who’d driven Dean crazy through the first half of freshman year in college. His voice was the paragon of sex, and he was beautiful. And he knew about Dean’s panty...thing.

Dean tried to calm himself down, ignoring Sam’s questioning stare and reminding himself that apparently Cas was a crossdresser. Which meant he wouldn’t make fun of Dean because, duh, hypocrisy.

Would Cas remember him? Maybe not. They’d only had one class together; only seen each other at that one party.

Fuck, Dean’s bad luck would never run out, would it?

“He’s just standing in the hall now,” Sam said, interrupting what had probably been a tense silence (Dean hadn’t been paying attention). “So hurry up with the pasta and get it on the table.” He walked to the refrigerator, taking out three beers and somehow managing to grasp them all within one monstrous hand. Dean’s brother was a fucking giant. 

“Yeah, yeah. Get out of my kitchen, you heathen. Garlic bread’s in the oven so come back and get it while I mix the pasta with the sauce.” Sam obeyed, disappearing back out into the hall. 

Dean could make out Sam saying “the kitchen’s this way,” as he no doubt led Cas to the table. 

Shit, was Cas allergic to basil? Sam would’ve said something, right? 

Dean knew he was wasting time thinking of all the different ways dinner could go wrong, but a belated paranoia had set in with the revealing of Cas’s true identity.

Whatever. It was just dinner. Cas probably wouldn’t recognize him. It had been almost nine years ago; really it was ridiculous that Dean even remembered it.

He finished mixing the pesto with the pasta and smiled. Not a bad dinner. “Sammy!” he called. “Garlic bread, you ass.” he carried the meal into the kitchen and avoided looking Castiel in the eye, setting down the bowl and then sliding into his seat. Sam huffed at Dean but quickly returned to the kitchen to take out the garlic bread.

“I’m Dean, by the way,” he introduced himself. It felt redundant. “Sam’s brother.” He finally looked up at Cas and inhaled sharply at the clear eyes that were focused on him. Dean let his gaze wander, if only to escape the intent stare that he didn’t want to stay caught in. Castiel was every bit as attractive as he had been in college, only now he was more filled out, less boyish in his appearance (in spite of his choice of dress). The oversized sweater the other man wore had slid down one shoulder, revealing part of his collarbone. His headband would have looked ridiculous on anyone else, but on Cas it provided a feeling of whimsy that made Dean’s stomach knot. 

Sam returned and smiled at his brother and Cas, who still hadn’t spoken in response. Castiel seemed to unfreeze at Sam’s return.

“Sam,” he smiled up at his host. “Thanks to you and your brother” --he looked briefly to Dean-- “for having me tonight.” He turned to Dean once more. “I’ve been told you’re an excellent cook.” he informed Dean. 

“Don’t get too excited,” Dean answered with a smile, playing off on the comment to hide his pride. “You’ll have to judge for yourself.” He served everyone, then they passed around the basket of garlic bread. 

“I feel like we’re at Olive Garden,” Sam commented.

“Well, I know I treat you like family, anyways.” Dean smirked back. Then he looked back at Castiel, gauging the other man’s reaction to the food. 

“You’re an exceptional cook,” Cas praised. “This is delicious. I haven’t had such a wonderful home-cooked meal since before college.”

Dean smiled bashfully. “Thanks.” Then he moved the conversation on quickly: “So, what do you do for a living?” As much as he’d wanted to change topics, he was also genuinely curious.

“I have a degree in business, but nowadays I wait tables and work as a barista at my brother’s coffee shop, mostly. I’ve had job interviews here and there, but most people are appalled by my sense of fashion” --he vaguely gestured at his headband-- “or my lack of ‘people skills.’” 

Dean bit back a grin at the disdainful way Castiel had said “people skills,” as though it was something he was glad to be lacking in. He’d wondered if Cas had stayed in business through college; he knew the other man had been thinking of switching to graphic design. Castiel was watching Dean again. 

“I know you,” he told Dean decisively.

Well, the jig was up. He’d remembered after all.

**Notes for the Chapter:**

> All mistakes are mine, I assure you-- if anything I've written offends any parties, please let me know! Chapter title means "from the heart" in Latin, and I'm sorry my writing is structurally... off. I don't know why I write like that. I need to work on fixing it, hence the writing of this fic. Oh yeah, and sorry this is short if anyone actually pays attention to this story? I love everyone who's reading it by the way, so... yes. Thanks to all!


	3. A Priori

**Notes for the Chapter:**

> I'm sorry I didn't update immediately ;_; As usual, critique would be appreciated, and to the people that already commented-- nnnnnnn thank you soooo much wow thank you thank you thank you. As for characterization, feel free to correct me? like, always? I need help, teach me how to write and characterize and everything I need to learn. If you don't want to get a bad rep by saying something mean, do it anonymously on my tumblr like go ahead insult me all you want just tell me so I know! My tumblr is castiel-sans-heaven. Also, I really don't have a set direction for this, I just have some scenes in my head that I want to happen. This chapter is even shorter than the last one, sorry T.T [end ramble]

Castiel’s suspicions were confirmed when he laid eyes on Dean. The same gold-flecked eyes and male-model face met his view when he sat down. His expression was earnest, his lips curved up in a hesitant smile.

He internally debated mentioning anything to the man, until the more daring aspect of his personality at last won out and he shared that he recognized Dean. (He immediately regretted it upon seeing Dean’s eyebrows push together in an expression of concern, his mouth a set line, countenance pensive.) 

Cas didn’t look away from Dean, seeing from the edge of his vision that Sam was glancing between them with an uneasy (albeit curious) half-smile.

“Really?” Sam prompted, focusing on Cas. Reluctantly, Cas turned away from Dean to meet Sam’s eyes, nodding. 

“In college…” he trailed off, shrugging. How would he explain why he remembered someone who was only in one class with him, and for only one semester? Perhaps he shouldn’t have said anything.

Dean looked vaguely horrified, but looked down to conceal his reaction from Sam. Then he looked back up, and Cas met his eye.

“Yeah,” Dean agreed. “We had an English course together.”

“Mm,” Cas hummed, “English is rather ambiguous. It was a poetry course.”

This redirected the subject somewhat, and Dean’s face colored in embarrassment. Sam’s face displayed a mixture of shock and amazement. 

“Did you--” Castiel looked between the brothers. Had he overshared? (Well, he knew that he’d done that by admitting he remembered Dean. He likened it to digging his own grave.) “Did your brother not know?”

Dean’s gaze flickers back to Cas. “Well, I didn’t tell him much about New York, since I switched in the second semester. But, that was…” he paused, searching for the right word. “It was personal. I hadn’t really. I dunno. Sorry I didn’t tell you Sam.”

A thin layer of polite friendliness was all that concealed the awkwardness that had filled every space between the three of them, and Castiel inwardly chastised himself. Why had he said anything?

“I’m sorry, Dean,” he offered after a moment. “I didn’t mean to overstep a boundary.”

“Nah, it’s cool. So, since we’re all revealing college experiences, did you ever go through with the wing tattoos?” Dean quirked his lips into a smirk, and Cas wondered briefly if it was a defense to hide what he was really thinking. Then, Castiel blinked.

“You remember that?” he asked in surprise. 

“Yeah, your wrist tattoo is fucking sweet, how could I forget? You said you wanted wings someday.” Dean shrugged. “I always liked tattoos, so I was interested. Wings are badass.” 

Then Cas smiled down at his plate, fork twisting and catching tendrils of noodle. “No” he said softly. “I ended up balking at the last minute. I still want them, but.” He sighed. “I was scared, and nobody tried encouraging me. But I guess that’s okay, since big tattoos aren’t always easy to cover.”

“Hmm, bummer,” Dean nodded. “But I don’t blame you.” 

Sam looked between them, looking somewhat lost. “Wow, you guys seem to know each other better than I’d expected. Were you good friends or what?”

Both other men looked up to Sam with near matching expressions of alarm. Hastily, Dean answered, “We didn’t hang out much, but we crossed paths all the time at parties, and we partnered up once or twice.” Then he shrugged vaguely. 

_____________________

Now that Dean mentioned it, Cas remembered that they had worked together.

It was a big assignment, too. How could he have forgotten? It was one of his best (and simultaneously worst) memories of himself with Dean. It was supposed to be a collaboration. Unconventional was putting it mildly. They’d needed to write separate poems, without discussing anything with each other beforehand. The professor hadn’t told anyone initially, so the poems done were all personal-- unrelated. 

Then, they were partnered up and told to invent an epic poem (of sorts) about the two different “protagonists” of the different poems. For one thing, it was invasive. Many of the poems written were deeply personal, not meant to be shared with classmates. But there Cas had found himself, preparing to bare his soul to Dean through his writing, and to receive the same in return. 

Castiel had written about his fall from grace. His protagonist, an ethereal fictionalization of himself, was a wandering soul with a guilt-ridden past. The two pieces of their respective works had fit together divinely, through luck and perfect matching (on the professor’s part). 

Dean had written about a condemned man, and Cas wondered if it was symbolic of Dean’s own life, but didn’t dare ask. The man Dean had beautifully described was living in a hell invented by his own mind, restricted by what he’d grown up believing.

They decided to write about how the two characters pieced each other together through understanding. It had been Dean’s suggestion, and Castiel recalled how excited he was that Dean had thought up such a perfect way to bring together the two halves of the story. 

Each of their separate poems were how the characters had felt before finding each other.

It was that, and the fact that they’d gotten a great grade on it, which made Castiel define it as a favorite among his recollections of Dean.

However, Castiel had made the mistake of asking Dean what the poem meant for them. Dean had insisted that it was only a poem, that he’d only provided the idea for the sake of the grade. Castiel had been hoping intently that it might mean something else.

It had been stupid to be so hopeful, he realized upon Dean’s response, and as Castiel finished recalling the ordeal, he also remembered why he’d tried so hard to forget it. 

___________________________

“Cas?” Sam asked, looking at his friend with an expression of concern. Castiel had fallen silent, and the awkwardness that had seemed to pass was right back in place. 

The other man blinked, then met Sam’s gaze. “My apologies,” he said sheepishly. “I just… remembered something. Nothing important.”

“Oh, okay,” Sam said unsurely. He raised an eyebrow at Cas, who shook his head slightly to dismiss any reason for the other man to be worried. 

Then, Sam glanced at his watch. “Shit. I hate to eat and run like this, but I don’t want to be late to--” 

“Yeah, yeah, just go. I’ve got it covered, and Cas is cool.” Dean waved Sam away, urging his brother to leave. “Have fun, treat Jess nicely, don’t be cheap, you hear?” 

Sam nodded, rolling his eyes and grabbing his plate. He disappeared into the kitchen, then called a hasty goodbye from the doorway as he left.

“Some host,” Dean snorted. Castiel smiled.

“Your brother his very kind. Thank you for having me. I should be leaving, as well. I’d hate to overstay my welcome and make things...awkward.” he said to the older Winchester.

“Don’t worry about making things awkward,” Dean answered with a grin. “I do that enough on my own, I don’t mind. Besides, it’s nice to see you. I liked you, in college. I was bummed we didn’t stay in touch. Sorry about that.”

Castiel’s eyebrows knit together in concentration at Dean’s words. Did he mean that? 

“Oh, it’s fine,” he said after a moment, realizing that he’d let an uncomfortable silence settle once more. “It seems we’ve found each other again anyways.”

Dean smiled at that. “Yeah, we did. So, Sam didn’t really elaborate but he said I could ask you and I’m curious. Why the” --he gestured at Castiel’s clothing-- “I don’t know how to say it without being an asshole. But, like, the flower headband and the girly sweater and stuff. The crossdressing.”

Castiel looked up at Dean, smirking. “That’s why,” he said (totally not cryptically). “You described the sweater as girly. I’m not trying to antagonize you, but I dress the way I do because I don’t like the fact that gender roles in our society extend even to our choice of dress. Why should apparel define gender or sexuality? It’s stupid.”

“That’s awesome,” Dean commended the other man. “I didn’t mean to offend you, by the way, if I did. Dude, that’s. That’s great.”

Castiel smiled, suddenly feeling self-conscious. “Thanks. And you didn’t offend me. I’m glad you aren’t close-minded. Some people tell me I offend them when they see me, and you-- you’re doing the opposite.”

“Wow, anyone offended by your great sense of fashion is a total douche. Sucks to be them.”

___________________

Sam opened the passenger door of his Dodge, smiling at Jess. “You look beautiful,” he told her sincerely. She smiled at him.

“You’re too kind, Sam,” she answered. “So what’s the plan for tonight, anyways?”

Sam shrugged at her sheepishly. “I wasn’t sure what to plan, I just knew I wanted to see you. Is that cheesy?”

“Yes,” she told him, laughing. “But it’s also really romantic and cute, so I forgive you. Why don’t we go see a movie or something?” 

“That sounds like the perfect date,” Sam agreed. “I missed you.”

She kissed his cheek as he pulled onto the busy street. “I missed you, too, dork. 

It was maybe a little lame, and stupidly domestic, but Sam loved every second of it.


	4. Bona Fide

**Notes for the Chapter:**

> I'm sorry this took 134567890 years! I've been busy with other things, blah. As always, comments are appreciated, and thanks to any and all that have stuck around!!

Castiel had stayed much later than he’d expected, he and Dean reminiscing over their college experiences together. It had been pleasant, and had resulted in them exchanging numbers. They’d glossed over the initial awkwardness, pleasing Cas infinitely. 

The day after the dinner, Sam had caught Cas at the coffee shop. Sam interrogated Cas on the subject of His Relationship With Dean, until he concluded that nothing particularly terrible had occurred while he was on his date.

Dean and Cas had exchanged cell phone numbers (Castiel denying himself the right to be pleased-- it was merely out of courtesy, right?) at the evening’s end, Dean pointing out that they’d lost touch before and should share them in case they ever wanted to reconnect. Or something. Cas couldn’t care less, honestly: he had Dean Winchester’s phone number.

Not that he ever worked up the courage to text or call the other man, but still. It was the sentiment behind it that Castiel valued. The idea that Dean had willingly provided a means of contact for Castiel. 

He didn’t expect to be Dean’s waiter six days following the dinner, but there were only so many waiters available on a Friday night, and in fairness, the restaurant was high quality.

So Castiel waited on Dean during the man in question’s dinner date. (Castiel was definitely not disappointed that Dean was on a date. Why would he care? They’d barely been acquaintances in college. Cas had no right to cling to Dean or his social life.) 

The woman, who had bright red hair and sly eyes, looked at him and grinned. “Hi,” she’d greeted him. Castiel wasn’t used to people who enthusiastically greeted their waiters, but she seemed harmless enough.

“Hello,” he’d answered with a smile. “My name is Cas, and I’ll be your waiter for the night. Are you waiting for someone?”

“Yeah, my dork of a dinner date is running late, probably. But what else is new?” she laughed, and Castiel continued to smile at her, unsure of what else to do. 

“Can I take your drink order, at least?” he asked. She smiled. 

“Shirley temple-- you’re never too old for one of those, right? God, I love eating here.” she grinned at him. 

Cas nodded. “Appetizers?”

She shook her head. “I think I’ll wait for Dean.”

Dean. Why was it always Dean? Castiel felt compelled to ask if she meant Dean Winchester, but decided not to. He’d obviously find out soon enough.

“Should I come back in a few minutes?” he inquired politely. She started to nod, then stopped. 

“No, I see him! I’m sorry, he’ll be over in a few seconds, no doubt.” Charlie stood up, waving at someone behind Castiel, who turned in curiosity.

Dean grinned at Charlie then glanced back up at Cas, and raised his eyebrows.

“Cas,” he managed. “Hey, again.”

“Hi. I’m-- your waiter tonight… I understand if you’d prefer someone else, but we’re short staffed tonight…”

“Don’t worry about it, man, I like you.” Dean laughed, then slid into the chair opposite Charlie.

Charlie wiggled her eyebrows at Dean suggestively. 

“Are you the mysterious Castiel?” she asked. Cas felt himself blush, and nodded. “Oh my god, Dean,” she enthused, “it’s obviously fate. I feel like such a cockblock.”

Castiel would have asked what that meant, but he was there to serve them, not interfere with their date. “I’m sorry, Dean, I didn’t mean to cause trouble… can I take your drink order?”

“Yeah, yeah,” Dean shot his companion a glare. “I’ll take a beer. Whatever’s on tap is fine, thanks.”

Castiel nodded in response and left to get drinks for the pair.

___________________________

“So, Dean, was that the infamous Castiel?” Charlie teased, giving him a significant look. Dean scowled. 

“Yeah, that was Cas, but no, I’m not letting you say it like that. Jesus, Charlie.” 

“Ha, yeah, he was cute. Maybe cuter in a dress.” 

Dean glowered at his friend. “I wouldn’t know,” he retorted. Charlie just laughed at him. 

“Whatever, he seems cool. I think it’s really awesome, you know, why he doesn’t let gender normatives define him. Like, whoa, genius! Anyways, what do you think you’re gonna order?” 

“Nice segway,” Dean answered sarcastically. “I heard the alfredo here is great, I’ll probably get that.”

Castiel returned a few minutes later, drinks in hand. Charlie accepted her soft drink excitedly and Dean rolled his eyes at her. 

“She’s a five year old,” Dean stage whispered to Cas, who smiled softly at the banter between them. 

“Is this your first date?” he asked, his voice taking on an odd tone. Dean looked at Cas, puzzled, then laughed upon realizing what the other man meant.

“Oh my god, no!” Charlie huffed, giggling. “I’ve got a girlfriend. Besides, nowadays Dean’s not much interested in us ladies.” She shrugged. Dean flushed.

“Yeah,” he nodded to Cas, “Charlie’s just a good friend of mine. Haven’t seen her in awhile, wanted to catch up. Aren’t you supposed to be waiting on us, though? I didn’t think interrogation came with the meal.” 

Castiel paled. “My apologies,” he said sheepishly. Dean shook his head and dismissed it with the wave of his hand. 

“Kidding, relax.” he shrugged. “I think we’re ready to order…?” He glanced to Charlie for confirmation, and she nodded. They placed their orders and Cas was off again.

“Dude, you have to seduce him. He’s so cute!” Charlie marveled. 

“Yeah, he’s cute, but I don’t think he’s into me. Also, things were kind of weird at dinner.” Dean looked at the table, avoiding Charlie’s questioning gaze.

“Weird how? ...or why?” 

“Well, we knew each other in college. We were, sort of friends I guess? We worked on this awesome collaborative project and hung out occasionally, but right before I transfered something really awkward happened at a party and I can’t tell if he remembers or not. I don’t know if I freaked him out or what, but it’s just kind of...awkward.” 

“Wow, smooth. Well, he seems pretty chill about things so it’s worth a shot, isn’t it? I mean, you haven’t really been in a real relationship since Victor, and that was months ago.” she pointed out. 

“Maybe. But I don’t want things to go wrong and affect his friendship with Sam. They’re pals, now, you know? It’d be. I don’t know, It’d be weirder.”

Charlie smiled reassuringly. “I’m sure things’ll work out, whatever you decide.”  
____________________________

After Dean and Charlie left, Cas tried not to think too hard on what Charlie had said. That “Dean’s not much interested” in women. Did that mean he wasn’t straight? Castiel had simply assumed as much judging by his various relationships in the semester he’d known the other man: Rhonda Hurley, Lisa Braedan, and a variety of other girls Castiel never bothered to learn the names of. Never had he seen Dean with another man. 

Not that it was Cas’s place to judge, obviously. 

He decided to call Sam about it. After all, he liked to think they were close enough friends for Cas to ask about his brother without raising too many questions.

“Hello?”

“Hello, Sam.”

“Oh, hey, Cas. What’s up?”

Castiel sighed. How could he ask what he wanted without divulging too much information about why he wanted to know. “I ran into your brother earlier, when he was out to dinner.”

“Oh?” Sam asked. It seemed as though he wasn't sure what Cas wanted to know. 

“Yes. I was wondering about something his companion said… she implied that Dean wasn't… heterosexual.” He trailed off hesitantly, and he heard Sam’s laugh on the other end.

“Believe me, he’s not. I mean, he likes to keep up an appearance of hypermasculinity, but it’s total bullshit. When he was younger, he kind of struggled with coming to terms with himself, I think. Honestly, it probably had something to do with our dad. Is that why you called? He’s single, you know.”

Castiel flushed pink, cursing himself for being so blatant. “Oh, okay, I’m sorry to have pried I was just curious. Um, goodbye.” He hung up and chastised himself silently for his insolence. 

At least he’d gotten his answer, he reasoned as he undressed and prepared for bed.


	5. Tempus Fugit

**Notes for the Chapter:**

> I'm so sorry to anyone following the story T.T This took me forever to write and it still doesn't feel like it fits but whatever. I kind of got slammed with personal issues and finals but I stayed home today and had time to sort the chapter as best I could. Thanks to all who stuck around and feedback's always appreciated!! <3

A month passed, and throughout it Cas encountered Dean on various occasions. Without fail, Dean always greeted Castiel with a smile and wave, never staring at Castiel’s outfits or pretending not to know him. It was pleasant, and Castiel began to internally think of Dean as a friend again. 

It eventually occurred to Cas that he would have run into Dean sooner than the dinner with him and Sam, if Dean had been living with Sam for long. He became determined to find out where Dean had been, if only to put his wandering mind to rest.

Dean and Sam came for coffee one day, together, and Cas decided to risk asking them together as he took Dean’s order (Sam’s having been prepared already, courtesy of Gabriel). 

“You haven’t been in California long, have you?” he asked quietly as he added a dash of eggnog in the spirit of Christmas. 

“No,” Dean admitted, watching the other man. “I stayed in New York for a long time. Spent some time in Kansas, where I grew up, but I ended up out here. What can I say? I missed my brother.” He shrugged. “What about you? How’d you get out here?”

“Gabriel offered, after my other family members excommunicated me on account of my ‘lifestyle,’” Castiel rolled his eyes and gestured to their location. “It’s also probably why I don’t have a more impressive job, but I’m not going to change just to conform. That’s idiotic.” 

Dean grinned. “You’re really damn stubborn,” he remarked. Castiel shrugged in response, not denying the statement. “I’m sorry you have a family compiled of complete asswipes. Their loss, not keeping you in their lives.” 

Castiel smiled at that. “Thank you. I appreciate it.”

_____________________

As time bled on, their friendship became more solid. The pair occasionally texted each other, and sometimes they would get coffee when Castiel’s shift ended at the shop. Both of them enjoyed the company, but of course neither of them did anything to further the relationship. After all, it was odd enough that they’d known each other so long ago and then found each other again-- it seemed neither wanted to risk losing the other once more by acting on their feelings.

Dean was startled awake one morning by the rattling of his cell phone vibrating against the nightstand where he’d set it. After some fumbling (and swearing), Dean managed to get a hold of it and answer the call.

“What?” he asked, voice rough with sleep and tone disgruntled.

“Dean-o,” came a familiar voice. “Morning, sunshine. Sleep well?’

“Gabe?” Dean asked, accusing. “How the fuck did you get my number?” He climbed out of bed reluctantly, kicking the sheets away from where they’d tangled about his legs.

“I’m nosy and Castiel’s horrible at keeping track of his cell. Speaking of my little bro, I have a big favor to ask involving him. If you do it, coffee’s on the house for two weeks.”

Dean squinted, rubbing his eyes and opening the kitchen cupboard in search of anything edible. “What kind of a favor needs that kind or bribery? What do you need?”

“Well, aren’t you just the liveliest,” Gabriel said sarcastically. “Anyways, Cassie’s sick. Pretty sure he could vomit up a lung at any moment, and he’s, like, barely lucid. I don’t want to leave him alone but I really have to go to work. I mean, I’m late to open up already anyways, and I’m short staffed ‘cause Cas is obviously out. So could you help me out and stay with Cas?”

“You know I work, right?” Dean poured cereal into a bowl and slumped into a seat. 

“Sure, whatever. What do you even do?”

“Jesus Christ,” Dean flailed a hand exasperatedly, glaring at his cereal. “I told you when I got the job, man. Adler’s company its sister company, remember?”

“Wait, seriously? Zachariah Adler, that piece of shit homophobe?”

“Yeah. He’s too high up for me, though, so my bosses are all pretty okay. He likes to meet with some of his staff and he does job interviews sometimes, but he didn’t do mine. That’s totally irrelevant, though. I can stay with Cas if you really intend to hold up your end of the bargain, but I don’t know Cas’s address.”

“Ah, thank you Dean. You’re a life saver! I’ll text you the address, and Cas should be able to buzz you up. If he says anything weird, it’s ‘cause I gave him some medicine a few minutes ago and he gets...loopy.”

Dean rolled his eyes. “You’re helpful. Okay, I’ll be over soon and you can just go now, open up.”

____________________

It was freezing inside Castiel’s apartment, which was the first thing Dean observed. The second was that Cas was only wearing a skimpy nightgown with pink lace at the hem. Wow, okay.

“Cas,” Dean greeted. Castiel smiled, and something about the other man’s grin was different from usual. It was less reserved, more stretched and eager.

“Dean! You came!” Cas reached out to Dean, making grabby hands for Dean. He was standing on the couch, which was facing the television. He had one knee propped against the back cushion of the couch.

“Jeez, Cas, I didn’t realize you were a monkey,” Dean muttered. He stepped forward, kicked off his boots and walked over to Castiel, putting one hand against the top of the couch’s back. Castiel leaned forward, dropping down so he was kneeling on the couch. 

“Sit with me?” The man asked hopefully, looking at Dean. Reluctantly, Dean walked around the side of the couch and climbed onto it to sit with Cas, who grinned. “Thank you.”

He leaned his head against Dean’s shoulder affectionately, and Dean closed his eyes. This was...weird.

“So, you had medicine and now you’ve loosened up, I see.” he commented finally, opening one eye to look at Cas. 

“Yeah,” Castiel nodded back, dragging out the word like an exhaled breath. “Gabriel left you a note. You aren’t dating him, right? I don’t want you to-- date my brother.” He stood up, stumbling a little as he escaped the lumpy couch, and reached for Dean. “You should see the note, Dean.”

Dean followed obediently, trying not to think too hard on how Castiel had laced his fingers with his own. 

“Thanks, man,” Dean patted his friend’s shoulder once they reached the kitchen table. Sure enough, a note had been left for him. The note offered instructions on when to give Castiel the medicine and a bolded THANKS, DEAN, but little else. Certainly no explanation about why Castiel behaved so oddly. 

“Do you like Gabriel?” Castiel asked, looking at Dean with round eyes. “Are you two dating? Did you not tell me?”

“God, no, we aren’t dating,” Dean immediately assured, making a face. “Why don’t you lay down, sleep off the weird medicine?” 

“Yeah,” Cas agreed with a slow nod. “Bedroom.” He pulled Dean toward the other side of the kitchen, where it broke off into other rooms. “My room’s here.” Together they entered Castiel’s bedroom, and Cas flung himself onto the bed. “Sleep, please, stay,” he mumbled, face smushed into the pillow. Dean rolled his eyes but followed Cas, tentatively sitting at the bed’s edge. “Want to go dress shopping--have a boyfriend. Dean, it’ so mundane.” Castiel’s complaints were half-formed, nonsensical and slurred but sincere judging by his tone. “So bored.”

“You’re more than bored, you’re high on cough medicine.” Dean answered. “If you promise to take a nap right now, I’ll take you dress shopping when you feel better, okay? I’ll buy whatever you pick, and you can wear it on a date with your awesome boyfriend, okay?”

Castiel nodded, turning his head so he could look at Dean. “Yes, please.” Then he closed his eyes and sighed.

Dean doubted Cas would remember this. He made the executive decision not to give Cas the next dose of whatever Gabriel had thought to be a good thing to give his sick brother. Clearly, it hadn’t helped do anything except encourage Castiel’s feverish behavior. 

He pulled one of the blankets at the edge of the bed up, unfolding it and tossing it over Castiel’s shivering form. The guy had passed out, thank god. Dean wasn’t sure how’d he’d have dealt with a drugged Cas.

______________________

Castiel woke up in his bed, his head throbbing with the dull ache of a head cold but his body clammy with the feel of a fever. Gross. He sat up slowly, running a hand through his ruffled hair. How had he gotten there? He could have sworn he had just been puking his guts up in front of Gabriel in the kitchen…

“Hello?” he called softly, his throat parched. He coughed, then repeated, louder, “hello?” After a beat, “Gabriel? Are you still here?”

He heard rustling and sank back down and closed his eyes, relieved. Gabriel hadn’t left him. A figure entered the room quickly, pressing a cool hand to his forehead, and Cas sighed. “Gabe, did you tell everyone you’re closed?”

“Um, no… he didn’t. He left to open, actually.” The voice, rough and familiar, was definitely not Gabriel’s.

“Dean?” Castiel asked, trying not to voice his surprise.

“Your brother called me. How’re you feeling, by the way?”

“Like shit,” Castiel sighed. “I’m sorry you have to endure this. You can go home, I’ll be fine.”

“Nah, dude, relax. This is fine. You said some gibberish when I got here but you passed out like, two seconds later. I made soup, hope that’s okay. I had to raid your fridge.”

“Oh god, I did? What’d I say?” Castiel asked, horrified. “Wait, you made--? That’s more than okay… ah, wow, thank you.” He reached to grab Dean’s wrist as the other man began to move away. “I mean it, that means a lot.”

“Anytime,” Dean smiled, “no problem. Why don’t you eat something? It’ll make you feel better. And don’t worry about what you said. Nothing important, rest assured,” he laughed. 

“Okay,” Castiel nodded. He pushed the blanket off of himself and stood up slowly, closing his eyes as the world began to spin. “Ow.” 

Dean offered a hand, and Castiel took it gingerly, following Dean’s guidance and ignoring the heat of his face and neck that had nothing to do with a fever.


	6. Dei Gratia

**Notes for the Chapter:**

> hOLY SHIT I AM SO SORRY!! I didn't mean for there to be this ridiculous time gap in updating and I'm gonna try to be more regular with it until it's finished :( Some stuff came up that kept me away then i was uninspired for a bit but now i think I know where I'm taking it... thank you so much to everyone who's left comments and criticism and kudos!! You're all so kind ????? ? ? like you don't understand how great you all are so thank you so much <3

Dean had reluctantly doled out another dose of pills to Cas at Gabriel’s insistence that day, and Cas had mumbled one other thing to him. “I remember,” he’d slurred. “In college... was inspiration.”

(And whatever that had meant, Dean refused to dwell on.) 

________________

Sam thought he and Jess should meddle. Jess was smarter than that. 

“We can’t,” she insisted, her tone admonishing. Sam looked at her pleadingly, and she rolled her eyes at him. Pathetic.

“You’re insufferable, you know that?” she teased, poking him. He grinned back, raising his eyebrows at her hopefully.

“Is it a go? Please? They’re obviously in love with each other. It’s freaking ridiculous!” He waved his hands to emphasize, and she folded her arms over her chest, disapproving. 

“Whatever’s going on between your secret BFF and your brother, isn’t our place. They’ll deal. Relax.” She dismissed her boyfriend’s urging easily. 

“Cas literally asked me if Dean was straight. He even had the decency to sound sheepish. We owe it to them to tamper at least a little, don’t you think?” Sam prodded. Jess only shook her head in response. Sam whined, “come on, Jess! They’re perfect for each other. Dean’s lonely! Could I at least tell him Cas obviously has a crush on him?”

“Oh my god, Sam,” Jess huffed, laughing. “Fine, go ahead and tell him. But I had nothing to do with it, understand?”

Sam nodded back, grinning widely, then texted his brother. 

\--so u & cas are friends now? -4:27 pm

A moment later, Dean responded.

\\\what’s it to you, samsquatch -4:27 pm

\--i think cas likes you -4:28 pm

Dean’s answer came delayed, Sam noted. 

\\\of course he does. everybody likes me- i’m awesome! -4:31 pm

\--no i mean like a crush. i think he has *feelings* for you -4:32 pm

\\\why do you text like a thirteen year old? -4:32 pm

\--you’re avoiding the subject, jerk -4:33 pm

\\\whatever, bitch -4:34 pm

\--i’m serious, though! dean, he’s head over heels for you. he asked if you were straight -4:35 pm

\\\that’s great sammy. -4:35 pm

\--that’s great??? is that seriously all you have to say? do you reciprocate or what? -4:36

\\\not having a gay-ass feelings talk with you -4:37 pm

\--oh my GOD dean get over yourself. work it out with cas, alright? he’s obviously into you -4:37 pm

Sam rolled his eyes at Dean’s childishness as he sent his last text. Then he glanced up at Jess. “I told him,” he announced, grinning. Jess shook her head at him.

“I hope they hurry up and get together, so we can go on double dates,” she smirked. (Sam couldn’t agree more.)

________________

It was welcome information, in Dean’s opinion. He was fairly certain that nobody shamelessly stared at their friend without it being at least slightly more than platonic. Not that he would dare mention that to Cas. It’s not like he minded, anyways. It was...cute. 

Since Cas had evidently talked about Dean behind his back with Sam, Dean reasoned that it wouldn’t hurt to do the same with Gabriel. He found the older Novak with relative ease, catching him at Trickster Treat just as he was closing for the evening. 

“Hey, Gabe, can we talk?” Gabriel turned at the sound of Dean’s voice, smirking at the taller man.

“That’s kinda what we’re doing right now, isn’t it, Dean-o?”

Dean frowned. “Hilarious,” he retorted sarcastically. “I meant about Cas.”

“Shit, what’d he do this time? Honestly, he probably didn’t mean to offend you, he just doesn’t really have a filter and--”

“Dude, what the fuck? No, he didn’t do anything wrong!” Dean managed to halt Gabriel’s rush of words, huffing a laugh at Gabriel’s wide-eyed, concerned expression. “What would he have even done?”

“Nevermind,” Gabriel dismissed awkwardly, avoiding Dean’s narrow gaze. “What did you want to say?” he snapped, glaring back. 

Dean finally relented. “Fine, be that way, jackass. I was wondering if Cas had...feelings for anyone.”

“Ooh, jealous? Didn’t peg you as the type!” Gabe’s shit-eating grin was downright horrifying, Dean observed with a grimace.

“I’m not jealous, you dick. I was asking because Sam’s convinced he’s in love with someone and I doubt it.”

“Depends on the someone,” Gabriel raised an eyebrow suggestively at Dean, still grinning. “I think he wants you to ravage his innocent-flower self.”

“Dude, gross.” Dean deflected the vulgarity of Gabriel’s words rather than addressing the meaning behind them. “I’m not gonna ravage your brother. But I really do want to know.”

“Yeah he’s definitely infatuated. But, I mean, if you’re not interested--which is hilarious, by the way, because you so totally are interested--then he’ll understand. Or, you know, he’ll try to. And he’ll pretend it’s okay.”  
Dean nodded at Gabriel’s explanation. “I’m going on your word, ‘cause he’s your brother, not Sam’s. I’ll talk to Cas, I guess.”

Gabriel waved him off with the threat of kicking him out of the coffee shop if Castiel ever learned of the conversation. Dean pretended to be concerned. 

________________

There was a noticeable shift in Dean and Castiel’s relationship after the day Dean spent taking care of Cas. It was so evident that the two men in question hadn’t needed the help of siblings to show it to them. The problem was that neither of them were willing to address it.

It was time to change that. Dean reasoned that if he asked Castiel out formally, the worst that could happen was Cas would politely reject him. Obviously, the guy was too thoughtful to act disgusted, and Dean knew he wasn’t homophobic (no brainer), so their friendship wasn’t exactly at risk. Besides, it wouldn’t hurt to seize the opportunity before it faded. Things always seemed to elude Dean when he wanted them most.

So Dean decided to text Cas. 

\\\hey, cas, you around? -5:12 pm

//Yes, why? -5:13 pm

Dean took a moment to gather all of his courage, then typed back:

\\\i was wondering if you’re doing anything tonight. -5:14 pm

//What do you mean? I only have my usual plans. (That is, none.) -5:14

Dean grinned to himself at Castiel’s wry humor.

\\\would you be interested in getting dinner with me? -5:15

After a beat, he sent a second text.

\\\as a date, i mean. -5:15 pm

There was a long span of time between Dean’s text and Castiel’s response, and Dean panicked. Maybe it had made Castiel uncomfortable? Eventually though, Dean’s phone vibrated with a new message and he looked at it eagerly.

//Do you mean it? -5:20 pm

\\\of course i do! unless you’d rather not? i’m sorry if i made you uncomfortable -5:21 pm

//No! You didn’t make me uncomfortable! I didn’t think you were interested in me, though. I would love to. -5:23 pm

Dean couldn’t help the rush of excitement that washed over him at Castiel’s answer. The date was a go!

\\\awesome. what time should i get you? -5:24 pm

//Would thirty minutes from now be too soon? -5:25 pm

\\\6 is fine! get you at the apartment? -5:25 pm

//Yes, please. I look forward to seeing you. :) -5:26 pm

________________

Castiel was gorgeous. It was the first thing Dean thought when he laid eyes on the other man, whose hair was ruffled in its usual manner of bedhead-gone-right. He was wearing jeans and a plain, long-sleeved black shirt with a grey knit poncho. Dean wanted to touch it and see if it was as soft to the touch as it looked, but he refrained in favor of grinning at Cas. He smiled back pleasantly at Dean.

“You ready to go?” Dean asked, stepping away from the doorway slightly. Castiel nodded, stepping forward as Dean moved back so that they were both in the hallway. He closed the door behind him.

“Do you have a place in mind?” Castiel asked curiously as they walked to the elevator together. Dean shrugged in response. 

“I was thinking we could get something at the mall, if that’s alright. This is kinda weird, but-- when you were sick, and out of it, you know? You said you wanted to go shopping, and I promised I’d take you. I don’t know if you remember, but--” he shrugged again “--I’d hate to break a promise.”

Castiel looked at Dean, brow furrowed as he thought. “I don’t…” he started, trailing off right after the second word escaped his lips. “I remember,” he whispered, as if surprised by himself. “You-- you mean that?”

“Of course. It’ll be fun! We can wander around, maybe catch a movie or something.” Dean smiled at Cas cheerfully, and Cas nodded in response.

“That sounds like a wonderful evening.”

“And that’s what it’s gonna be!” 

______________

It was. (Cas paid for dinner, so in exchange Dean bought Cas a casual summer dress-- as promised. He wondered if he’d ever seen a smile as bright as Cas’.)


	7. NOT A CHAPTER

**Summary for the Chapter:**

> THIS IS NOT A NEW CHAPTER

I AM SO SORRY TO EVERYONE FOLLOWING THIS

I AM TEMPORARILY ABANDONING THIS WORK (I'll probably come back to it at some point, re-work it so it flows more smoothly, finish it up, etc.) UNTIL FURTHER NOTICE  
School work, personal life, and the Supernatural Femslash Minibang all take precedence over this work of writing (which was more of a writing exercise than anything else, anyways)  
I'm so sorry to everyone following this, seriously... I hope to finish it someday and make it a better, more worthy read for anyone who followed it.  
Thank you for reading it up to here!! I love you all.


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